Hydrochloric Acid → 2-(2-Iodophenyl)propanamide

HRID 592353노트

반응식

HRID 592353 반응식
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9](O)=[O:10].CC[N:15](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.C(=O)([O-])[O-].[NH4+].[NH4+]>C1COCC1.CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:15])=[O:10]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 517111Ammonium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222368512-(2-Iodophenyl)propanoic acid

생성물 1

HCID 867122772-(2-Iodophenyl)propanamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-(2-iodophenyl)propanoic acid (9.73 g, 35.2 mmol) in THF (24 mL), DMF (4 mL) and DIPEA (30.7 mL, 0.176 mol) was stirred with HOBt (7.14 g, 52.9 mmol) and EDCl.HCl (10.1 g, 52.9 mmol) for 10 minutes at room temperature under N2. Ammonium carbonate (16.9 g, 0.176 mol) was then added and the reaction mixture was stirred overnight at room temperature. The volatiles were removed under reduced pressure before sat. aq. NaHCO3 (100 mL) was added to the residue. The aqueous phase was extracted with EtOAc (3×100 mL) and the combined organics were washed with brine, dried over MgSO4 and the volatiles were removed in vacuo to give the impure title compound I13 as a pale yellow solid (˜95% purity, 10.05 g, >95%). LCMS-D: rt 3.12 min; m/z 276 [M+H]+.

후처리

  1. customThe volatiles were removed under reduced pressure before sat. aq. NaHCO3 (100 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted with EtOAc (3×100 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe volatiles were removed in vacuo

출처 및 근거

ORD 기록
ord-c331bba519b8463eaa897cac4789a061
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238644B2

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